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Tetraaryldiborane(4) Can Emit Dual Fluorescence Responding to the Structural Change around the B–B Bond

Yoshiaki Shoji, Naoki Tanaka, Yasuhiro Ikabata, Hayato Sakai, Taku Hasobe, Norbert Koch, Hiromi Nakai, Takanori Fukushima

2021Angewandte Chemie International Edition12 citationsDOI

Abstract

Abstract We report the successful synthesis of tetramesityldiborane(4) (Mes 4 B 2 ) through the reductive coupling of a dimesitylborinium ion. Owing to the steric protection conferred by the mesityl groups, Mes 4 B 2 shows exceptional chemical stability and remains intact in water. Single‐crystal X‐ray analysis revealed that Mes 4 B 2 has an orthogonal geometry, where the B–B center is completely hidden by the mesityl groups. Remarkably, Mes 4 B 2 emits dual fluorescence at 460 and 620 nm, both in solution and in the solid state. Theoretical calculations showed that Mes 4 B 2 in the excited S 1 state adopts a twisted or planar geometry, which is responsible for the shorter‐ or longer‐wavelength fluorescence, respectively. The intensity ratio of the dual fluorescence is sensitive to the viscosity of the medium, which suggests that Mes 4 B 2 has potential as a ratiometric viscosity sensor.

Topics & Concepts

FluorescenceSteric effectsChemistryExcited statePhotochemistryViscosityWavelengthIonCrystallographyMaterials scienceStereochemistryAtomic physicsOpticsOrganic chemistryOptoelectronicsPhysicsComposite materialLuminescence and Fluorescent MaterialsOrganoboron and organosilicon chemistryBoron Compounds in Chemistry
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